(2S,3S,4S,5S)-3,4-dibenzyloxy-2,4-dimethyl-5-ethyl-2-triisopropylsiloxymethyltetrahydrofuran

Base Information

Chemical Name:(2S,3S,4S,5S)-3,4-dibenzyloxy-2,4-dimethyl-5-ethyl-2-triisopropylsiloxymethyltetrahydrofuran
CAS No.:548487-92-9
Molecular Formula:C₃₂H₅₀O₄Si
Molecular Weight:526.832
Hs Code.:

Synonyms:(2S,3S,4S,5S)-3,4-dibenzyloxy-2,4-dimethyl-5-ethyl-2-triisopropylsiloxymethyltetrahydrofuran

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Chemical Property of (2S,3S,4S,5S)-3,4-dibenzyloxy-2,4-dimethyl-5-ethyl-2-triisopropylsiloxymethyltetrahydrofuran

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Technology Process of (2S,3S,4S,5S)-3,4-dibenzyloxy-2,4-dimethyl-5-ethyl-2-triisopropylsiloxymethyltetrahydrofuran

There total 7 articles about (2S,3S,4S,5S)-3,4-dibenzyloxy-2,4-dimethyl-5-ethyl-2-triisopropylsiloxymethyltetrahydrofuran which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 96.0%

: 100-39-0
benzyl bromide

: 548487-94-1
(2S,3S,4S,5S)-2,4-dimethyl-3,4-dihydroxy-5-ethyl-2-triisopropylsiloxymethyltetrahydrofuran

: 548487-92-9
(2S,3S,4S,5S)-3,4-dibenzyloxy-2,4-dimethyl-5-ethyl-2-triisopropylsiloxymethyltetrahydrofuran

Guidance literature:: (2S,3S,4S,5S)-2,4-dimethyl-3,4-dihydroxy-5-ethyl-2-triisopropylsiloxymethyltetrahydrofuran; With sodium hydride; In N,N-dimethyl-formamide; at 0 ℃; for 0.5h;

benzyl bromide; With tetra-(n-butyl)ammonium iodide; In N,N-dimethyl-formamide; at 0 - 23 ℃; for 12h;
DOI:10.1021/ja034865z

Reference yield:

: 548488-20-6
(2S,3S,4S,5S)-4-dimethylphenylsilyl-3-hydroxy-2-hydroxymethyl-2,4-dimethyl-5-ethyltetrahydrofuran

: 548487-92-9
(2S,3S,4S,5S)-3,4-dibenzyloxy-2,4-dimethyl-5-ethyl-2-triisopropylsiloxymethyltetrahydrofuran

Guidance literature:: Multi-step reaction with 5 steps

1.1: NaH / dimethylformamide / 0.5 h / 0 °C

1.2: 96 percent / n-Bu₄NI / hexane; dimethylformamide / 12 h / 0 - 23 °C

2.1: 85 percent / cumene hydroperoxide; KH; NMP / n-Bu₄NF / tetrahydrofuran / 40 h / 23 °C

3.1: 98 percent / H₂ / Pd/C / ethanol / 24 h / 760 Torr

4.1: 96 percent / imidazole / dimethylformamide / 12 h / 23 °C

5.1: NaH / dimethylformamide / 0.5 h / 0 °C

5.2: 96 percent / n-Bu₄NI / dimethylformamide / 12 h / 0 - 23 °C

With 1H-imidazole; 1-methyl-pyrrolidin-2-one; Cumene hydroperoxide; hydrogen; potassium hydride; sodium hydride; palladium on activated charcoal; tetrabutyl ammonium fluoride; In tetrahydrofuran; ethanol; N,N-dimethyl-formamide;
DOI:10.1021/ja034865z

Reference yield:

: 548487-91-8
(2S,3S,4S,5S)-3-benzyloxy-2-benzyloxymethyl-2,4-dimethyl-5-ethyl-4-hydroxytetrahydrofuran

: 548487-92-9
(2S,3S,4S,5S)-3,4-dibenzyloxy-2,4-dimethyl-5-ethyl-2-triisopropylsiloxymethyltetrahydrofuran

Guidance literature:: Multi-step reaction with 3 steps

1.1: 98 percent / H₂ / Pd/C / ethanol / 24 h / 760 Torr

2.1: 96 percent / imidazole / dimethylformamide / 12 h / 23 °C

3.1: NaH / dimethylformamide / 0.5 h / 0 °C

3.2: 96 percent / n-Bu₄NI / dimethylformamide / 12 h / 0 - 23 °C

With 1H-imidazole; hydrogen; sodium hydride; palladium on activated charcoal; In ethanol; N,N-dimethyl-formamide;
DOI:10.1021/ja034865z